A facile one-pot, solvent-free synthesis of new pyrazolone-1,3-dithiolan hybrids through the reaction between 2-pyrazoline-5-ones, CS₂, and α-chloroacetaldehyde

Abstract

An efficient one-pot, solvent-free synthesis of pyrazolone-1,3-dithiolan hybrid derivatives from the reaction of 2-pyrazoline-5-ones, carbon disulfide, and α-chloroacetaldehyde in the presence of triethylamine is reported. Two possible stereoisomers (E and Z) can be formed in this reaction. The structures of the produced 5-pyrazolone-1,3-dithiolan derivatives are determined based on their IR, ¹H NMR, ¹³C NMR, and mass spectroscopic data. The 4-hydroxy-1,3-dithiolan moieties in hybrid products 2a and 2 g are readily converted to the related dehydrated products 3a and 3 g, respectively.

GRAPHICAL ABSTRACT

KEYWORDS:

• Hybrid molecules
• Solvent-free reactions
• Green chemistry
• Pyrazolones
• 1,3-Dithiolanes

Disclosure statement

No potential conflict of interest was reported by the author(s).

Supporting information

¹H NMR, ¹³C NMR, and Mass spectra of all new compounds associated with this article can be found in the online version.

Additional information

Funding

Financial support of this research by University of Mohaghegh Ardabili, Iran, is gratefully acknowledged.